CN1180848A - 新的光致抗蚀剂共聚物 - Google Patents
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Abstract
本发明公开了一种用于亚微米光刻术的光致抗蚀剂树脂共聚物(如式Ⅰ所示),及一种包括此共聚物的光致抗蚀剂组合物:其中R1是含有0—30个碳原子的烷基;R2和R3互不相关地分别为含有1—15个碳原子的烷氧基或环烷氧基;R4和R5互不相关地分别为氢或烷基;及p,q和r可相同或不同,每一个是从0至90的聚合比例。
Description
本发明涉及一种适用于高集成度半导体器件的亚微米光刻术的光致抗蚀剂共聚物，特别是本发明涉及一种由戊二酰亚胺衍生物和丙烯酸衍生物所形成的光致抗蚀剂共聚物，其具有高抗蚀性和耐热性。本发明还涉及一种含有这些共聚物的光致抗蚀剂组合物。
最近以来，化学放大(chemical amplification)的光致抗蚀剂已被广泛应用于半导体器件上，这是因为发现这些光致抗蚀剂对DUV(深紫外线)光(现已被认为是一种适合完成半导体器件高度集成的光源)具有高度的敏感性。化学放大光致抗蚀剂一般是由光酸产生剂及聚合物基质所组成，该聚合物基质具有可敏感地和酸反应的化学结构。
此光致抗蚀剂的机制如下：当此光致抗蚀剂通过掩膜曝露在DUV光源下时，因光酸产生剂(photoacid generator)的作用而产生质子，然后质子和聚合物基质的主链或侧链反应。此反应可转换此共聚物的结构如使之分解、交联或改变其极性。因而异常地增加了此共聚物在显影溶液中的溶解度。因此，当以显影溶液处理时，共聚物在曝光区溶解，而在未曝光区不溶解，在基板上留下掩膜形状的正影像。
在光刻术中光源的分辨率及波长的关系为如下式所示：
R＝kxλ/NA
其中R是分辨率，k是一程序常数；λ是光源的波长；及NA是数值孔径。如公式所示，愈短的光源波长可形成愈细的图形。
所以，研究已趋向发现适合于改善分辨率的新光源，结果开发出了将半导体器件集成至1G或更高尺寸规模的DUV光源。现在使用DUV光源的例子包括氟化氪准分子激光器(之后称作“KrF”)和氟化氩准分子激光器(之后称作“ArF”)，波长分别为248nm和193nm。后者光源被用于4G或更高尺寸规模的DRAM。依据所发现的新光源，所以必须开发出一种合适的光致抗蚀剂薄膜。
一般而言，光致抗蚀剂必须是高抗蚀的和高耐热的。为了改善抗蚀性，通常必须找出芳香系树脂；然而，因为芳香系树脂在短波长时显示出高吸收度，所以照射光酸产生剂的光能量减少，因此产生质子的机会减少。
在使用短波长光源像ArF的情况下，使用聚(甲基丙烯酸甲酯)(PMMA)树脂，而不使用芳香系树脂。然而，PMMA树脂实际应用非常难，这是因为其抗蚀性和耐热性差的缘故。
本发明的目的之一在于克服现有技术中碰到的上述困难，及提供一种新的共聚物，其能用作采用ArF作光源的亚微米光刻术的光致抗蚀剂树脂，且其在抗蚀性和耐热性方面是优异的。
本发明的另一目的在于提供一种用作光致抗蚀剂树脂的新共聚物，其可高分辨度和敏感度地进行构图。
本发明的又一目的在于提供一种适用于高集成度半导体器件的光致抗蚀剂组合物。
本发明涉及一种光致抗蚀剂共聚物，由以下的结构式I所表示：
R1是含0-30个碳原子的直链或支链烷基；
R2和R3互不相关地分别为含1-15个经取代或未经取代碳原子的直链或支链烷氧基或环烷氧基；
R4和R5互不相关地分别为氢或烷基；
p，q和r(其可相同或不同)分别为从0至90的聚合比例。
较佳的式I共聚物为式II的共聚物；式II
其中
R1是式II的烷基；
其中x，y和z(其可相同或不同)分别为不超过5的整数。
关于R2和R3更详细的说明为下式III代表的烷氧基。
R4和R5互不相关地分别为氢或烷基，及
p，q和r(其可相同或不同)分别为一从0至90的聚合比例。
式III
聚合比例p，q和r是依据加入至聚合反应中的单体量确定的。
本发明的新共聚物是由戊二酰亚胺衍生物和丙烯酸衍生物所构成，可依据常规的自由基聚合技术，使用自由基聚合引发剂生产而得。
其可以在本体聚合反应或溶液聚合反应中进行聚合，所使用的聚合溶剂可单独的为环己酮、甲乙酮、苯、甲苯、二恶烷、二甲基甲酰胺，或其组合物。通常此聚合反应是在聚合引发剂如过氧化苯甲酰、2，2-偶氮双异丁腈(AIBN)、过氧化乙酰、月桂基过氧化物或叔丁基过乙酸酯的存在下进行的。
用于在半导体器件上形成正微细图形的正光致抗蚀剂组合物可以一般的方式，在有机溶剂中将此新颖的式I光致抗蚀剂共聚物和光酸产生剂混合而得。关于配方，此共聚物的量取决于有机溶剂、光酸产生剂及光刻术条件，较佳的量为所用有机溶剂重量的约5-40％。具有相同于结构式I中的R2和/或R3的化合物可选择性地作为溶解抑制剂加入。
为了制备光致抗蚀剂，首先将本发明的共聚物溶于环己酮中，溶入量为10-30％(重量)，加入相当于此光致抗蚀剂聚合物重量约0.2－10％的鎓盐或有机磺酸作为光酸产生剂。然后以一超细过滤器过滤此溶液而产生—光致抗蚀剂溶液。
将此光致抗蚀剂溶液旋转涂覆在硅晶片上，然后在烤箱中或热板上以80-150℃的温度软性烘烤1-5分钟；采用分步重复，利用深UV光或准分子激光器作光源进行曝光程序。之后，使所述晶片在温度100-200℃下进行后烘烤步骤，再将经此后烘烤过的该晶片浸入2.38％TMAH溶液中90秒，可得到一超精细正抗蚀剂影像。
如前所述，由本发明新颖共聚物制备而得的光致抗蚀剂由于其抗蚀性及耐热性高，所以可涂覆成厚1.0μm或更薄，因此在分辨率和焦点深度上可获得满意的结果。
虽然为说明的目的已对本发明的较佳实方案进行了公开，然而本领域的技术人员能在不偏离所附权利要求公开的本发明精神及范围的情况下作各种改变、增加及替换。
Claims (3)
1.一种光致抗蚀剂共聚物，由下式I所代表：
R1是一含有0-30个碳原子的直链或支链烷基；R2和R3互不相关地分别为含有1-15个经取代或未经取代碳原子的直链或支链烷氧基或环烷氧基；R4和R5互不相关地分别为氢或烷基；p，q和r可相同或不同，分别为从0至90的聚合比例。
2.如权利要求1的光致抗蚀剂共聚物，其中所述的R1选自下式II所示的烷基：其中x，y和z可相同或不同，分别为一不超过5的整数，及所述的R2和R3互不相关地分别为选自下式III所示的烷氧基：
3.一种光致抗蚀剂组合物，包括下式I的共聚物：
R1是含有0-30个碳原子的直链或支链烷基；R2和R3互不相关地分别为含有1-15个经取代或未经取代碳原子的直链或支链烷氧基或环烷氧基；R4和R5互不相关地分别为氢或烷基；p，q和r可相同或不同，分别为从0至90的聚合比例。
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1019960047901A KR100211546B1 (ko) | 1996-10-24 | 1996-10-24 | 신규한 포토레지스트용 공중합체 |
| KR47901/1996 | 1996-10-24 |
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| CN1180848A true CN1180848A (zh) | 1998-05-06 |
| CN1099052C CN1099052C (zh) | 2003-01-15 |
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| CN97119099A Expired - Fee Related CN1099052C (zh) | 1996-10-24 | 1997-10-24 | 光致抗蚀剂共聚物及其组合物 |
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| US (1) | US5981142A (zh) |
| JP (1) | JP3147059B2 (zh) |
| KR (1) | KR100211546B1 (zh) |
| CN (1) | CN1099052C (zh) |
| DE (1) | DE19746932B4 (zh) |
| FR (1) | FR2755137B1 (zh) |
| GB (1) | GB2318579B (zh) |
| NL (1) | NL1007343C2 (zh) |
| TW (1) | TW449673B (zh) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103189932A (zh) * | 2010-12-30 | 2013-07-03 | Lg化学株式会社 | 电极以及包括该电极的电子器件 |
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| US5380337A (en) * | 1994-01-24 | 1995-01-10 | Romaine; Richard A. | Mesh-type skin biopsy appliance |
| KR100200305B1 (ko) * | 1996-06-29 | 1999-06-15 | 김영환 | 원자외선용 감광막 및 이를 이용한 감광막패턴형성방법 |
| KR100263906B1 (ko) * | 1998-06-02 | 2000-09-01 | 윤종용 | 백본이 환상구조를 가지는 감광성 폴리머 및 이를 포함하는 레지스트 조성물 |
| KR100642830B1 (ko) * | 2004-08-25 | 2006-11-10 | 주식회사 삼양이엠에스 | 양성 레지스트 조성물 |
| KR100597715B1 (ko) * | 2004-08-25 | 2006-07-10 | 주식회사 삼양이엠에스 | 음성 레지스트 조성물 |
| US7873058B2 (en) * | 2004-11-08 | 2011-01-18 | Mosaid Technologies Incorporated | Outlet with analog signal adapter, a method for use thereof and a network using said outlet |
| KR20080020605A (ko) * | 2005-05-30 | 2008-03-05 | 가부시키가이샤 가네카 | 수지 조성물 |
| EP3761114A4 (en) * | 2018-02-28 | 2021-04-07 | FUJIFILM Corporation | ACTIVE LIGHT SENSITIVE OR RADIATION SENSITIVE RESIN COMPOSITION, RESIST FILM, PATTERN FORMATION METHOD, METHOD OF MANUFACTURING ELECTRONIC DEVICE, AND RESIN |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3964908A (en) * | 1975-09-22 | 1976-06-22 | International Business Machines Corporation | Positive resists containing dimethylglutarimide units |
| US4246374A (en) * | 1979-04-23 | 1981-01-20 | Rohm And Haas Company | Imidized acrylic polymers |
| US4524121A (en) * | 1983-11-21 | 1985-06-18 | Rohm And Haas Company | Positive photoresists containing preformed polyglutarimide polymer |
| US4569897A (en) * | 1984-01-16 | 1986-02-11 | Rohm And Haas Company | Negative photoresist compositions with polyglutarimide polymer |
| US4837124A (en) * | 1986-02-24 | 1989-06-06 | Hoechst Celanese Corporation | High resolution photoresist of imide containing polymers |
| US5019488A (en) * | 1988-09-29 | 1991-05-28 | Hoechst Celanese Corporation | Method of producing an image reversal negative photoresist having a photo-labile blocked imide |
| JP2875556B2 (ja) * | 1989-10-11 | 1999-03-31 | 沖電気工業株式会社 | 半導体素子の製造方法 |
| JPH0459864A (ja) * | 1990-06-29 | 1992-02-26 | Sumitomo Chem Co Ltd | 熱可塑性樹脂組成物 |
| US5227280A (en) * | 1991-09-04 | 1993-07-13 | International Business Machines Corporation | Resists with enhanced sensitivity and contrast |
| FR2696469B1 (fr) * | 1992-10-02 | 1994-12-02 | Atochem Elf Sa | Procédé de préparation de copolymères glutarimides et composés intermédiaires utiles. |
| JPH08286384A (ja) * | 1995-04-14 | 1996-11-01 | Hitachi Ltd | パタン形成方法及びそれに用いるフォトレジスト材料 |
| US5879853A (en) * | 1996-01-18 | 1999-03-09 | Kabushiki Kaisha Toshiba | Top antireflective coating material and its process for DUV and VUV lithography systems |
-
1996
- 1996-10-24 KR KR1019960047901A patent/KR100211546B1/ko not_active IP Right Cessation
-
1997
- 1997-10-18 TW TW086115348A patent/TW449673B/zh not_active IP Right Cessation
- 1997-10-21 US US08/954,871 patent/US5981142A/en not_active Expired - Fee Related
- 1997-10-22 FR FR9713244A patent/FR2755137B1/fr not_active Expired - Fee Related
- 1997-10-23 NL NL1007343A patent/NL1007343C2/nl not_active IP Right Cessation
- 1997-10-23 GB GB9722438A patent/GB2318579B/en not_active Expired - Lifetime
- 1997-10-23 DE DE19746932A patent/DE19746932B4/de not_active Expired - Fee Related
- 1997-10-23 JP JP30811697A patent/JP3147059B2/ja not_active Expired - Fee Related
- 1997-10-24 CN CN97119099A patent/CN1099052C/zh not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103189932A (zh) * | 2010-12-30 | 2013-07-03 | Lg化学株式会社 | 电极以及包括该电极的电子器件 |
| CN103189932B (zh) * | 2010-12-30 | 2018-06-15 | Lg化学株式会社 | 电极以及包括该电极的电子器件 |
Also Published As
| Publication number | Publication date |
|---|---|
| NL1007343A1 (nl) | 1998-04-27 |
| DE19746932A1 (de) | 1998-04-30 |
| DE19746932B4 (de) | 2006-05-18 |
| GB2318579A (en) | 1998-04-29 |
| GB2318579B (en) | 2000-09-13 |
| NL1007343C2 (nl) | 1998-06-08 |
| JP3147059B2 (ja) | 2001-03-19 |
| GB9722438D0 (en) | 1997-12-24 |
| FR2755137B1 (fr) | 1999-07-16 |
| FR2755137A1 (fr) | 1998-04-30 |
| KR19980028733A (ko) | 1998-07-15 |
| JPH10133380A (ja) | 1998-05-22 |
| KR100211546B1 (ko) | 1999-08-02 |
| CN1099052C (zh) | 2003-01-15 |
| US5981142A (en) | 1999-11-09 |
| TW449673B (en) | 2001-08-11 |
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